Triethylamine hydrochloride → HCID 66699625, compound

HRID 1818489Notes

Reaction equation

[C:1]([C:4]1[CH:33]=[CH:32][C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH:16]([O:25][CH:26]3[CH2:31][CH2:30][CH2:29][CH2:28][O:27]3)[C:17]3[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=3)[C:20]#[N:21])=[CH:12][CH:11]=2)=[C:6]([C:34]([F:37])([F:36])[F:35])[C:5]=1[OH:38])(=[O:3])[CH3:2].[N-:39]=[N+:40]=[N-:41].[Na+].Cl.C(N(CC)CC)C>>[OH:38][C:5]1[C:6]([C:34]([F:36])([F:35])[F:37])=[C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH:16]([O:25][CH:26]3[CH2:31][CH2:30][CH2:29][CH2:28][O:27]3)[C:17]3[CH:24]=[CH:23][CH:22]=[C:19]([C:20]4[N:39]=[N:40][NH:41][N:21]=4)[CH:18]=3)=[CH:12][CH:11]=2)[CH:32]=[CH:33][C:4]=1[C:1](=[O:3])[CH3:2]

Participants

Reactant 3

HCID 11130Triethylamine hydrochloride

HCID 33557Sodium Azide

HCID 57884410HCID 57884410, compound

Product 1

HCID 66699625HCID 66699625, compoundYield 96.2%

Procedure

Employing the procedure of Example 1 using 3-[[4-(4-acetyl-3-hydroxy-2-trifluoromethyl-phenoxymethyl)-phenyl]-(tetrahydro-pyran-2-yloxy)-methyl]-benzonitrile (384 mg, 0.731 mmol), sodium azide (475 mg, 7.31 mmol), and triethylamine hydrochloride (1.01 g, 7.31 mmol) to yield the title compound as a tan solid (400 mg, 96%): 1H NMR (CD3CN) 61.44-1.91 (m, 6H), 2.56 (s, 3H), 3.44 (m, 1H), 3.78 (m, 1H), 4.66 (q, 1H), 5.23 (d, 2H), 5.91 (d, 1H), 6.73 (dd, 1H), 7.39-7.62 (m, 5H), 7.89-8.08 (m, 3H), 13.75 (s, 1H).

Sources & evidence

ORD record: ord-b273394befa4405bbaa81cdbc2095b46
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07598423B2

Reaction notes

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